


The Mr. Square Bear Adventures

by sentencefragments



Category: Arrow (TV 2012)
Genre: Childhood Friends, F/M
Language: English
Status: Completed
Published: 2016-03-11
Updated: 2016-03-11
Packaged: 2018-05-26 03:59:07
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,644
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6222775
Author URL: https://archiveofourown.org/users/sentencefragments/pseuds/sentencefragments
Summary: <blockquote class="userstuff">
              <p>If re-gifting something you gave someone twenty five years ago is wrong, Oliver doesn’t want to be right.</p>
            </blockquote>





	The Mr. Square Bear Adventures

**Author's Note:**

  * For [everythingilove](https://archiveofourown.org/users/everythingilove/gifts).



 

He remembers the day he first met her. Barely, but he does. He was only five years old and it was the most exciting day of his short little life. The details are bit hazy, but his mom has told the story so many times that he doesn’t need her to fill in the blanks anymore.

It’s her birthday today. The woman he loves more than anything in this world is turning twenty five. It seems like a lifetime ago when they first met. For her, it literally is. For him, it almost is. It’s been twenty five years, to the day exact, since he met her and he’s about to do something he’s been dreaming about for a very long time. Looking over to his right, she’s still sleeping peacefully, curled around her pillow. The morning sun peeking through the curtains doesn’t have the same effect on her as it has on him. He’s a morning person, she prefers the night. He’s always the first one to wake up, out of bed in minutes to make the both of them some ridiculously delicious breakfast while she can barely say ‘good morning’ before at least one cup of coffee. She can come up with the most ingenious string of code way past midnight, while his brain runs on ‘relax-mode’ after dinner.

Her blonde curls are a mess as they fan out over the pillow and she twitches in her sleep, a tiny crease appearing between her eyebrows before it fades again. A small smile tugs at his lips. She is the most beautiful mess he’s ever seen.

* * *

 

He remembers being five years old, and getting to pick out a plushy toy for a girl he’d never met before. He remembers being excited about the endless choices but also confused because how was he supposed to know what she’d like. He remembers being captivated by the fluffy brown teddy bear with the big doe-y eyes. He remembers holding onto his mother’s hands as they walked down the hospital corridor. He remembers the excited high-pitched whispers as they stepped into a balloon-filled room. He remembers the wide smile on the face of the woman he knew as ‘aunt Donna’.

Moira met Donna in college. They were sorority sisters at SCU and best friends. Moira was a little older, in her junior year when Donna was a freshman, but the two were as close as biological sisters. After graduation, Moira married his dad, Robert and they had him not even nine months later. They were very young, but happy. Their family’s wealth helped a lot too.

While Moira raised her son, Donna dropped out of college to be with a guy, Noah, who she thought was the love of her life. The friendship between the two of them hit a rough patch, as Moira strongly disagreed with Donna’s decision to drop out of school. Donna and Noah got married in a wedding chapel in Vegas, and it wasn’t until three years later that Moira would see her friend again, this time heartbroken, and pregnant. Noah had left his wife and unborn daughter in the middle of night. He’d packed his things, taken the car and driven off. After a few days, Donna realized he wasn’t coming back and she packed a bag and got on a bus to Starling City, hoping that she hadn’t completely ruined her friendship with Moira, praying that she would forgive her. That’s how she ended up on the Queen’s doorstep with tearstained cheeks that night.

“Do you want to meet her, Oliver?” Aunt Donna whispered, a smile on her face.

He looked up at his mom, silently asking if it was okay. She smiled at him and nodded.

“It’s okay, honey.” She whispered. “C’mon I’ll help you up.”

She bent down in front of him and lifted him up on the edge of the bed. Curiously, he peeked into the little bundle of blankets aunt Donna was holding.

“Oliver, this is Felicity.” Donna whispered, shifting the newborn in her arms so Oliver could see her better.

“That’s a beautiful name.” His mom murmured, putting a hand on aunt Donna’s shoulder. “For a beautiful girl.”

Aunt Donna smiled, but there was sadness hidden in her eyes. “It means happiness. Thought I could use some of that right about now.”

“F’licily” Oliver muttered in an attempt to test out the name, immediately liking how the syllables rolled over his tongue, even if he was pronouncing it incorrectly.

Donna chuckled, smiling a little brighter and reaching out to ruffle his hair.

Oliver turned back to the bundle in her arms with a smile on his face.

The baby was tiny and pink with chubby cheeks and pouty lips and droopy eyes. She yawned, stretching out the smallest hand he’d ever seen. Eyes full of wonder, he reached out, letting the baby curl her fingers around one of his. Her grip was tight, making him smile and look up at aunt Donna, who smiled right back at him. This tiny little human had him mesmerized in mere seconds and he’d completely forgotten his troubles on if she would like the gift he’d picked out for her.

Felicity Smoak was already his favorite person in the whole world and she wasn’t even a day old.

Donna and Felicity stayed with the Queens for a while, until Donna was able to go back to work, to a new job as a barista at a coffee shop. They moved out to a cozy little apartment at the edge of the Glades near her place of employment when she’d saved up enough money so she didn’t have to worry about finances for a while and could afford a decent car. Moira and Robert still helped out a lot. They would drop by with groceries every once in a while and when Donna went to work, they looked after baby Felicity. (read: Raisa looked after baby Felicity and Oliver) They even set up a college fund for the little girl, after discussing it with Donna, of course. She was very adamant that she wanted to contribute to said fund too. She wanted to make sure her daughter would get a good education.

Felicity was smart, even as a baby. Her mental capacity developed faster than what was considered normal. She was talking in full sentences by the time she was two and a half. Even though there was a five year age difference between Oliver and Felicity, they became fast friends. And when Oliver found the fluffy brown teddy bear with the big doe-y eyes laying on his bedroom floor after Felicity had gone home one night, he knew that she would not be sleeping that night unless he brought it back. She was four years old and devastatingly attached to the toy Oliver had picked out for her when she was born.

“Mr. Square Bear!” She squealed when he pulled the stuffed animal out of his jacket standing on her doorstep later that night. He’d somehow convinced his mom to drive them over there to bring the bear to his home.

Little Felicity with two brunette pigtails practically launched herself into his arms, her pink glasses pressing into his shoulder.

“Thank you Oliver!” She whispered. “I thought I lost him.”

Standing in the doorway, Donna sighed seeing the two of them huddled together, Oliver knelt down in front of her little girl, hugging her tightly, the bear being squeezed somewhere between them. Felicity only had eyes for Oliver.

“Thank you so much for driving all the way over, Moira. You should’ve seen her face when she couldn’t find him.”

Moira smiled, a hand curling around her expanding stomach. She’d finally gotten pregnant again. “Oliver insisted we bring it over immediately.”

“That’s very thoughtful of him.” Donna chuckled.

The two women exchanged smiles before Moira turned to her son.

“Oliver, honey, we should get going, it’s getting late.” Moira said, putting a hand on Oliver’s shoulder.

“No!” Felicity whined. “please don’t go.”

“baby it’s way past your bedtime already, Oliver has to go home now.” Donna tried to calm her daughter down, running a hand over her hair.

“I don’t want him to go!” Felicity cried, bottom lip pushing out in a pout and tears welling up in her big blue eyes

“Oliver, please stay!” She begged him.

Oliver smiled. “It’s okay, you’ve got Mr. Square bear now. Him and me made a deal on the way over here. He’ll watch over you for me, make sure there are no monsters under your bed or in the closet and that nobody is gonna hurt you.”

Felicity seemed to accept that, sniffling a little, eyes searching his. “Promise me?”

“I promise.” Oliver smiled.

She hugged him real tight after that. “Okay then.” She murmured in a small voice. “I’ll miss you though.”

Oliver closed his eyes for a moment as he hugged her. “I’ll miss you too. We’ll go play soon okay?”

Felicity beamed at him. “Okay!”

The Smoak girls waved the Queens off after that, the stuffed bear tightly clutched in Felicity’s little arms. She slept with the thing in her arms every night. It was getting dirty and old and worn out but it was her most prized possession. No shiny new toy could compare and she couldn’t (read: wouldn’t) sleep without the ragged old thing tucked in next to her.

Oliver and Felicity were as thick as thieves but they fought like siblings, always chasing after each other. Oliver playfully pulled her pigtails. Felicity looked up to him, put him on a pedestal, always wanting to spend time with him.

When Thea was born, Oliver and Felicity fought over who got to hold her first, so they held her together. Felicity sitting between his legs as they held the little baby girl with no less than four hands. Felicity loved Thea like she was her own sister from the moment they met.

As they grew older, their interests changed and they slowly started drifting apart, the age gap between the two becoming a bigger issue. Oliver thought girls were stupid and yucky and Felicity started favoring the technical over Barbie dolls and princess dresses. Pre-teen Oliver called her a baby, making her cry and run to her room to pour her heart out to Mr. Square bear. Oliver apologized not long after that, because no matter how yucky or young she was, she was his best friend. Don’t tell Tommy he said that. Tommy is his best friend too, but that’s different.

Mr. Square bear became a vital part of her life. They had tea parties and playdates and scary nights and as she grew up those things changed into building computers, reading vampire novels and painting her nails. The bear became sort of a stand-in for Oliver. Whenever she needed to talk to somebody, she would talk to the stuffed animal, pretending she was talking to Oliver.

But her childish obsession with the toy faded, like those things do. Mr. Square became a prop in some far corner of her bedroom that she occasional noticed, when she was cleaning, contemplating whether or not to throw it out. She never did. She couldn’t quite put her finger on why, probably sentimentality, but she couldn’t give the bear to goodwill –if they even wanted it in its horrible raggedy condition—so she kept it on her shelf in between some of her favorite books. It wasn’t until high school that she really needed the bear again.

Oliver was off to college, and she missed him terribly. Now that they were both older, they had been growing closer again, petty teenage phases out of the way and all. They called each other pretty regularly, and Oliver somehow always knew when she needed a pick-me-up in the form of a cheesy joke over text message.

She was about sixteen when she had her first boyfriend, and her first break-up. She’d locked herself in her room, laying in her bed and staring at the ceiling, her eyes tracing the constellations of glow in the dark stars she and her mother had put up there when she was seven. She’d been crying a lot, it was stupid. She didn’t even like Barry that much. He was nice, sure, and smart and they had the same interests, but that was it. On paper, they were perfect for each other but there was nothing between them beyond friendship. No spark. No fireworks.

She stared at her phone for a long time, willing it to ring. Nothing happened. Of course it didn't. It wasn't like Oliver could somehow sense her heartbreak all the way across the country. Sighing, she took the small flip phone into her hand, staring at the digital clock on the top screen. 11:36 pm. That meant Oliver would be fast asleep already. Or partying. It didn't stop her from trying to reach him anyways. She really needed to hear his voice right about now. The phone rang and rang, and Felicity was about to hang up when Oliver finally picked up.

"Felicity?" He asked. "Is everything okay?"

Relief washed over her. "Yeah, I'm okay, I just really wanted to hear your voice."

"Mr. Square Bear finally get sick of you?" He teased.

Felicity groaned. "Ha-ha, very funny, Oliver. I’m never gonna live that down, am I?" 

Oliver chuckled. "Probably not. What's up?"  He asked, seeing through her white lie immediately. He knew she wasn’t okay. He always knew. Like he had some weird ‘Felicity’s sadness level’-radar or something.

Felicity's breath hitched. "Barry and I broke up."

Oliver sighed. "Oh Felicity, I'm sorry."

She shook her head. "I'm okay, it was a mutual decision, but it still kinda stings, you know. Thank you for picking up. I know how late it is in Boston."

Oliver let out a breathy laugh. "No problem, anything for my favorite girl, but I'm not exactly in Boston."

Felicity frowned, sitting up on her bed. "What?"

"I kinda dropped out." He confessed.

"Oliver..."  Felicity sighed. " what happened?"

"Mind if we talk about this in person? Look out of your window."

If her eyebrows could’ve lifted even on her forehead in that moment they would have. "Oliver, you can't be serious."

"Just do it."

She groaned, pushed off of her bed and made her way over to the windowsill, peeking through the thin curtains. There he was, five floors below on the sidewalk in front of her apartment building, nonchalantly leaning against his red convertible. Felicity rolled her eyes. "I can't believe you." She muttered into her phone when he spotted her and waved with that stupid grin on his face.

"I thought throwing rocks was a little too much." He chuckled.

"You're literally the only person in the world who would think this is a good idea."  She said, rolling her eyes.

"C'mon, I think we both deserve comfort Big Belly Burger."

"My mom is going to kill you."

He shrugged. "Totally worth the sacrifice."

Felicity sighed. She really needed this right now. Her best friend and some freaking burgers and shakes.

"Alright." She murmured. "But you're paying."

Oliver beamed up at her in the dim lighting of the street lanterns. "It's a date."

Felicity scoffed. "You wish. I'll be down in a minute."

 

Later they would argue over if that was indeed they're first date, or if that happened years later after Felicity graduated  college at twenty and Oliver finally found the courage to utter the words: "Would you like to go to dinner with me?"

She thought he was joking at first, because the two of them? They were practically siblings. But, even Felicity couldn’t deny the crush she'd seemingly always had on him. So, she accepted, and they'd been together ever since. Oliver still teases her about Mr. Square Bear, but that childhood friend had earned a well-deserved spot in their bedroom.

* * *

 

Mr. Square Bear plays a pivotal role in today’s activities. He’s been planning it for weeks. It’s personal, romantic and cheesy. Perfect.

Oliver leaned over, brushing her hair out of the way and pressed a kiss to her temple.

“Happy birthday, baby.” He whispered, trailing his lips along her jaw, peppering kisses everywhere they meet her soft skin.

In her drowsiness, Felicity smiled and hummed in appreciation.

“You stay in bed, I’ll go make you breakfast.” Oliver murmured, pressing one last kiss to the tip of her nose before slipping from between the sheets. Slipping on his boxers from last night he went to the bathroom to wash his face before heading towards the kitchen.

He prepared all of her favorites. Chocolate chip waffles with extra whip cream and strawberries, a freshly brewed French press full of coffee, her favorite mug with the string of code printed on it, a boiled egg for protein, a glass of milk and a small vase with a single rose in it.

Taking a deep breath to calm his nerves, he grabbed the neatly wrapped gift from the top shelf in one of the kitchen cabinets. Where Felicity would never, ever look. With the tray of food in one hand and the gift in the other, he made his way back to the bedroom.

“Hmm. That smells amazing.” Felicity sighed, rubbing her eyes and rolling over to look at him. “You have no idea how great it is to have a boyfriend who’s also a chef, but you’re gonna get me so fat.”

Oliver chuckled and smiled brightly at her, putting the tray down on his side of the bed. She had no idea how proud he was of her being the CEO of her own company; Smoak Technologies. “It’s only because I love you.”

He sat down, still only wearing his boxers, leaned over and reached for her for her face.

“Happy Birthday Felicity.” He whispered, staring into her eyes for a moment before closing the distance between their lips. Felicity smiled into the kiss, running her fingers through his hair at the back of his head. Their mouths moved against each other in perfect synchrony, they’d had a lot of practice, but it was like they were made for each other. Two puzzle piece that fit perfectly together.

“I really wanna continue this but the food you’ve so lovingly prepared for me is gonna get cold.” Felicity sighed, pulling away so she could catch her breath.

Oliver laughed and with one last peck he got up and grabbed the tray of food. Together, they nibbled on the waffles, drank their coffee and made a mess with the whip cream. With a lot of kissing-breaks of course. When all the food was gone, Oliver put the tray aside and reached for the gift. He moved to sit across from where she was leaning against the headboard, bright smile on her face.

“Oliver, I told you, I didn’t want you to buy me anything.” She sighed. “I have everything I need.”

Taking his hand, she squeezed it lightly, smiling gently.

“I didn’t buy you anything, I promise.”

Felicity narrowed her eyes a little. “Okay, now you’ve peaked my interest.”

With a chuckle, Oliver handed her the box, unknowingly holding his breath in nervousness. Felicity pursed her lips in anticipation as she lifted the lid off the neatly wrapped gift, eyes going wide and mouth falling open in a soft gasp as she saw what was inside.

“Mr. Square Bear!” She squealed. “I thought he got lost during the move!”

Oliver let out a breathy laugh as she pulled him into a unexpectedly tight hug. “I found him in one of the boxes in the attic a few weeks ago.”

Felicity pulled away to look at him, confusion on her face, eyebrows knit together. “A few weeks ago? Why would you wait that long to give him to me?”

Oliver smiled. “Take a closer look.” He said, gesturing at the raggedy old stuffed teddy bear.

Raising an eyebrow at him, Felicity pulled Mr. Square Bear out of the box and gasped.

“Oh my god.” She squeaked out, gaze moving back to Oliver, hand coming up to cover her mouth. Stitched to one of the bear’s paws was a beautiful sparkly ring.

Scooting a little closer, Oliver took Felicity’s hand and sighed.

“Felicity, twenty five years since we first met, and every day I fall in love with you more. You’re the most important person in my life, helped me realize that business wasn’t for me, for which I am forever grateful.” He paused to let out a chuckle. Felicity smiled, teary-eyed. She knew what was happening.

“From how protective you are of your employees to the way you organize our massive DVD collection. How you always forget to leave the bathroom door open after you shower to the little texts you send me when we’re apart. Even your peanut-allergy. I love everything about you and I want to spend the rest of my life with you.”

Oliver took a deep breath. “Will you marry me, Felicity Meghan Smoak?”

Felicity whimpered, happy tears leaking out of her eyes as she nodded excitedly, bright smile on her face.

“Yes?” Oliver asked.

Felicity laughed and nodded again. “Yes!! Of course I will” She flung her arms around his neck and kissed him passionately.

When they both had to come up for air, Oliver reached for the toy from their childhood and carefully ripped the single stitch the ring was attached with.

“It was my mother’s.” He whispered, holding it up in between them.

Felicity sighed. “It’s stunning.”

“May I?” Oliver asked, reaching for her hand.

Nodding, Felicity held her breath as her fiancé slid the most gorgeous ring she’d ever seen on her ring-finger before pulling him close again and showing him exactly how much she loved him.

They didn’t leave the bedroom all day.

And Moira owed Donna fifty bucks.

**Author's Note:**

> find me on tumblr: sentence-fragments  
> or on twitter: @felicitties


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